This application relates to certain ortho-carboxylate ester sulfonylureas which are useful as agricultural chemicals and in particular have high herbicidal activity while showing activity to certain crops.
U.S. Pat. No. 4,383,113 and U.S. Pat. No. 4,394,506 include the disclosure of o-alkoxycarbonylbenzenesulfonylureas.
U.S. Pat. No. 4,435,206 and U.S. Pat. No. 4,544,401 disclose pyridinesulfonylureas which may be substituted at the carbon adjacent to the sulfonylurea bridge by CO.sub.2 (C.sub.1 -C.sub.6 alkyl).
U.S. Pat. No. 4,481,029 discloses herbicidal o-alkoxycarbonylthiophenesulfonylureas.
European Pat. No. 95,925, published 12/7/83, discloses herbicidal pyrazolesulfonylureas containing ortho-carboxylic acid esters.
U.S. Pat. No. 4,661,147 discloses herbicidal sulfonylureas containing ortho-carboxylic esters, CO.sub.2 R.sub.1, wherein R.sub.1 is C.sub.2 -C.sub.5 alkyl, C.sub.4 alkenyl or C.sub.4 alkynyl substituted with one or two substituents selected from: OH, SH, OC(W.sub.1)R.sub.17, SC(O)R.sub.17, OC(W.sub.1)OR.sub.17, SC(O)OR.sub.17, OC(W.sub.1)NR.sub.8 R.sub.17, SC(O)NR.sub.8 R.sub.17, OC(W.sub.1)NH.sub.2, SC(O)NH.sub.2, OC(W.sub.1)NR.sub.8 A, OP(W.sub.1)(OR.sub.10).sub.2, SP(W.sub.1)(OR.sub.10).sub.2, OSO.sub.2 R.sub.17, OSO.sub.2 NR.sub.8 R.sub.17, OSi(R.sub.9).sub.2 R.sub.10, S(O).sub.n R.sub.7, NR.sub.7 R.sub.8, ##STR1##
U.S. Pat. No. 4,549,898, issued 10/29/85 (Swiss priority 6/14/82), discloses herbicidal sulfonylureas of formula ##STR2## wherein R.sub.2 includes H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen,
NO.sub.2, C.sub.1 -C.sub.3 alkoxy, C(W)R.sub.8, SO.sub.2 NR.sub.6 R.sub.7, S(O).sub.n -- PA1 C.sub.1 -C.sub.3 alkyl or COR.sub.9 ; PA1 R.sub.9 includes C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 alkenyloxy, C.sub.3 -C.sub.6 PA1 alkynyloxy, C.sub.2 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.4 cyanoalkoxy, PA1 C.sub.1 -C.sub.6 alkylthio, C.sub.3 -C.sub.6 alkenylthio, C.sub.3 -C.sub.6 PA1 alkynylthio, C.sub.5 -C.sub.6 cycloalkoxy, C.sub.4 -C.sub.7 cycloalkylalkoxy, NR.sub.6 R.sub.7 or alkoxyalkoxy. PA1 E is a single bond or --CH.sub.2 --; PA1 R is H or CH.sub.3 ; PA1 W is O or S; PA1 R.sup.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, PA1 CN, nitro, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 PA1 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, PA1 SCF.sub.2 H, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or C.sub.1 -C.sub.2 PA1 alkyl substituted with one C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, SH, SCH.sub.3, CN or OH; PA1 R.sup.2 is H, F, Cl, Br, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl or PA1 C.sub.1 -C.sub.2 alkoxy; PA1 R.sup.3 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.3 -C.sub.4 PA1 alkenyl, C.sub.3 -C.sub.4 alkynyl, CH.sub.2 CN, phenyl or phenyl substituted by F, Cl, CH.sub.3 or OCH.sub.3 ; PA1 n is 0 or 1; PA1 A is ##STR6## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, PA1 C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, PA1 C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, PA1 C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, PA1 di(C.sub.1 -C.sub.3 alkyl)amino or C.sub.3 -C.sub.5 cycloalkyl; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, PA1 C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, PA1 C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, PA1 C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 PA1 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, PA1 C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, azido, PA1 cyano, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, ##STR7## CH.sub.2 CN, CH.sub.2 CO.sub.2 CH.sub.3, CH.sub.2 OH or N(OCH.sub.3)CH.sub.3 ; PA1 m is 2 or 3; PA1 L.sub.1 and L.sub.2 are independently O or S; PA1 R.sub.a is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.b and R.sub.c are independently C.sub.1 -C.sub.3 alkyl; PA1 Z is CH or N; PA1 Z.sub.1 is CH or N; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sub.3 is H or CH.sub.3 ; PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; and PA1 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; PA1 (a) when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA1 (b) when X or Y is C.sub.1 haloalkoxy, then Z is CH; PA1 (c) X.sub.4 and Y.sub.4 are not simultaneously Cl; PA1 (d) when W is S, then R is H, A is A-1 and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or 1,3-dioxolan-2-yl; and PA1 (e) Q.sub.2, Q.sub.3 and Q.sub.4 are not simultaneously methyl. PA1 E is a single bond; and PA1 W is O. PA1 E is CH.sub.2 ; and PA1 W is O. PA1 X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, Cl, F, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; PA1 Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, ##STR8## OCF.sub.2 H, SCF.sub.2 H, OCF.sub.2 Br, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3 ; PA1 R.sub.a is H or CH.sub.3 ; and PA1 R.sub.b and R.sub.c are C.sub.1 -C.sub.2 alkyl. PA1 A is A-1; PA1 n is 0; PA1 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl or OCF.sub.2 H; and PA1 Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, CH(OCH.sub.3).sub.2 or cyclopropyl. PA1 R is H; PA1 R.sup.1 is H, CH.sub.3, CF.sub.3, Cl, CN, SCH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2, CH.sub.2 OCH.sub.3 or CH.sub.2 CN; PA1 R.sup.2 is H, Cl, Br, CH.sub.3 or OCH.sub.3 ; and PA1 R.sup.3 is H, CH.sub.3, CH.sub.2 CF.sub.3 or phenyl. PA1 J is as previously defined; and PA1 X.sub.a is NH.sub.2 or HNC(O)OC.sub.6 H.sub.5, which are useful as intermediates to herbicidal sulfonylureas.
None of these patents discloses inter alia o-alkoxycarbonylaromatic sulfonylureas wherein the o-alkoxy group terminates in N.sub.3, SCN or NO.sub.2.